I can hardly recall the times I was NOT self-employed, but I do recall that they were all miserable times. I don't think I respond well to taking orders from others...
I have been a small-boat builder (until the gas shortages of the 70's forced me out), a real estate broker (until the high interest rates of the early 80's made it difficult), a free-lance computer programmer (that lasted the longest) and the owner of a retail/custom fabrication business (until I retired). I only quit the programming gig because I was getting too old to keep up with the language changes. I liked everything I did enormously, although some of them were a struggle.
As you might be able to tell from the variety, I got into each of them almost accidentally according to circumstances. I had recently moved to Florida and was unhappy with the lack of jobs when I saw an ad offering the assets of the boat builder for sale. He was an older gentleman who wanted to retire, and I jumped right in. When I had to close it when the price of resin shot so high, I was really depressed, A friend of mine was thinking about taking the real estate course and I went along to keep her company.
I ended up with my own brokerage, specializing in listing vacant lots for sale. You'd have to be familiar with the Florida market, but our city had 82,000 vacant lots sold all over the world, and there was an active resale market. I tapped into that, and became the first realtor in the area to computerize the solicitation of listings. When high interest rates shut down the construction of new houses, and thus the sale of building lots, I discovered I could market my computer skills.
For the next 15 years, I set up systems and small networks for small businesses, sold computers until the discount stores took over that function, and wrote custom software solutions for small businesses. I was one of the few who specialized in decentralized microcomputers. I also wrote code for larger companies under subcontracts. One of my programs was used to manage an American Express data base; another is still being used to track and manage golfers' handicaps at a local golf course, so there was a wide spread.
At one point, I bought a small house in a commercial neighborhood to serve as my company headquarters. When my kids got older and went off to college, I decided to move my business into my house, and rented out the converted house. The folks who rented it started a unique business; they dispensed propane refills for small cylinders, mostly grills; and they sold parts to rebuild gas grills. They also sold a few upscale grills, but they were ahead of their market.
The owner died from cancer at only 40 years old. His widow tried to continue the business but struggled. In the meantime, I was getting tired of trying to keep up with ever more rapid changes in computer languages -- that's a young man's game, and I was 55 years old. When she decided to give up, I was ready to step in and take over her business.
We completely gutted the previous house and turned it into a nice showroom, added the newly popular stainless steel grills and other upscale BBQs, added accessories and grilling supplies with wood chunks and BBQ sauces, and extended the hours to get propane cylinders refilled. We did very well. Eventually, seeing the demand for custom outdoor patio kitchens, and unable to find subcontractors to construct them for us, we went into the cistom fabrication ourselves. I invented some unique ways to build the cabinets and islands.
I closed that business about 3 years ago. It was a surprise; I thought I'd be going on for a while. But, I had one employee leave, another became disabled and couldn't work, and the last one died. These were all family or friends, and all of us had figured out how to run the business together. I decided it was too much at age 63 to think about training new employees who might or might not be dependable, so I shut it down. It turned out to be good timing, because I came up with my own health problems not long after and couldn't have continued.
Likes and dislikes? More of the former; you learn that the latter is part of the price you pay. I liked being on control. I liked setting my own agenda. I liked the challenge of finding solutions that others had not thought of. I liked the independence. And, while I ran into occasional setbacks, I mostly liked the money.
But, being in business for yourself means LOTS of time. The average amount of time I spent was 70 to 100 hours per week. There is planning, bookkeeping, records, deadlines to be met, lost time to be made up, all kinds of things that tie you to the business. YOU are the ultimate stopgap; there is no one else who will step into the breach.
Bottom line: if I had to do it all over again, I would change nothing (unless I was granted a crystal ball that could foresee the future problems /forums/images/graemlins/wink.gif ).